Cyclic Aromatic Amino Acids with Constrained 1 and 2 Dihedral Angles
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The concept of topographic design of peptide neurotransmitters and hormones was pioneered by Hruby ( 1 , 2 ). When the design involved primarily constraint of the side chains of a peptide that has a well-defined backbone conformation, the term “topographic design on a stable template” was proposed ( 3 ). The side chain χ 1 of aromatic amino acids, such as Phe, Trp, Tyr, and His, can be constrained in either the gauche (−) or gauche (+) conformation by linking the nitrogen atom to the aromatic ring through a methylene bridge (Fig. 1 ).
Fig. 1. Principle of side-chain constraint for Phe, Trp, and His.
![[(1S)-1-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-(6-aminohexanoylamino)-3-phenylpropanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]hexanoyl]amino]-4-bromobutyl]boronic acid，Moligand™，阿拉丁](https://img1.dxycdn.com/p/s14/2024/0619/722/0483842343985733081.jpg!wh200)
